[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[NH:10]1[CH2:15][CH2:14][CH:13](C(O)=O)[CH2:12][CH2:11]1.O.[OH-].[K+].[C:22]1(C)C(C)=CC=CC=1>>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][C:22]([N:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)=[N:1][C:2]=2[CH:7]=12-Amino-4-chlorophenol (400 mg) and 4-piperidinecarboxylic acid (360 mg) were mixed with polyphosphate (2 g) in xylene (30 ml) and stirred with heating at 180° C. for 2 hours. After cooling to room temperature, the reaction was stopped by adding water. The filtrate was adjusted to pH 12 with 50% potassium hydroxide aqueous solution and extracted with methylene chloride. The organic layer was washed with saturated brine and dried with magnesium sulfate, and then the solvent was evaporated under a reduced pressure to obtain the title compound 5-chloro-2-(1-piperidyl)benzoxazole (218 mg).
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